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Organic Lab Reactions 272

Organic Lab Reactions 272 - INFLUENCE OF SUBSTITUENTS 267...

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INFLUENCE OF SUBSTITUENTS 267 Aminosulfonic acids of the naphthalene and biphenyl series also have been deaminated,* but the smoothness of the reaction cannot be esti- mated from the available experimental data. The influence of carboxyl and nitro groups as well as chlorine and bromine atoms has been the subject of systematic investigations. All these groups promote the replacement of the diazonium group by hydro- gen. Though the data do not lend themselves to broad generalizations, it appears that, in the main, the effect is at a peak when the group is situated ortho to the diazo group, is diminished somewhat in the meta position, and is weakest in the para position. This gradation is illustrated by the results obtained with the diazonium salts from the isomeric aminobenzoic acids. When the orthQ diazonium nitrate is treated with absolute ethanol only reduction occurs; **• M ethyl benzoate is obtained in 53% yield, f The diazonium acid sulfate derived from Mi-aminobenzoic acid is converted into a mixture of ethyl benzoate,
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